Original scientific paper

Ring Expansion of Thiazolidine and Nucleophilic Substitution in N-Acyl Derivatives of 6-Thia-3,8-diazabicyclo[3.2.1. ]octan-2-one

J. J. Herak ; Research Institute PLIVA, Zagreb , Croatia, Yugoslavia
M. Kovačević ; Research Institute PLIVA, Zagreb , Croatia, Yugoslavia
B. Gašpert ; Research Institute PLIVA, Zagreb , Croatia, Yugoslavia

Abstract

Reaction of N3,N8-diacyl 6-thia-3,8-diazabicyclo/3.2. l./octan-2-
-one (I) with PC15 or S02Cl2 gave 6-chloro substituted N2,N5-diacyl
7-thia-2,5-diazabicyclo/2.2.2./octan-3-one (II). Treatment of II with
water yielded the 6-hydroxy derivative (III) while reaction with
methanol gave the 6-methoxy derivative (IV). Under the same
reaction conditions the mono N8-acyl derivative (V) gave a mixture
of 6-substituted 7-thia-2,5-diazabicyclo/2.2.2./octan-3-one and 4-
-su bsti tuted 6-thia-3,8-diazabicyclo/3.2. l ./octan-2-one derivatives
(XIV and XV; VI and VII; VIII and IX). It was proposed that
ring expansion of thiazolidine and nucleophilic substitution occured
vi a the thiiranium ion XIII as a common intermediate.

Keywords

Hrčak ID:

194270

URI

https://hrcak.srce.hr/194270

Publication date:

1.9.1982.

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